- Synthesis of Polymethoxyflavonoids from Hesperidin and Naringin and their Antiproliferative Activity
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[Figure not available: see fulltext.] A series of polymethoxyflavonoids were synthesized via cleavage of the glycosidic bond, dehydrogenation, selective methylation, bromination, nucleophilic aromatic substitution, O-prenylation, Claisen–Schmidt aldol condensation, cyclization, and oxidation from very abundant and inexpensive natural flavonoids hesperidin and naringin. The in vitro antiproliferative activity of the synthesized compounds was evaluated against a panel of four human cancer cell lines (Aspc-1, HCT-116, HepG-2, and SUN-5) by the CellTiter-Glo assay. The results showed that some of synthesized compounds exhibited moderate to high antiproliferative activity. Among them, (2E)-1-(2-hydroxy-3,4,5,6-tetramethoxyphenyl)-3-(7-methoxy-1,3-benzodioxol-5-yl)prop-2-en-1-one was revealed to be the most active with IC50 values ranging from 10.35 to 13.89 μM against all four cancer cell lines, the IC50 value (10.35 μM) being below positive control cisplatin (12.36 μM) against HepG-2 cells.
- Jin, Zhizhong,Liu, Kexiong,Su, Liang,Wang, Qiuan
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- ISOLATION AND SYNTHESIS OF TWO NEW FLAVONES FROM CONOCLINIUM COELESTINUM
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Two new flavones, 3',4'-methylenedioxy-5,6,7,8,5'-pentamethoxyflavone and 5,7,4'-trihydroxy-6,3',5'-trimethoxyflavone, have been isolated from Conoclinium coelestinum.Final structure proof was accomplished by synthesis.Key Word Index - Conoclinium coelestinum; Compositae; Eupatorieae; flavones; 3',4'-methylenedioxy-5,6,7,8,5'-pentamethoxyflavone; 5,7,4'-trihydroxy-6,3',5'-trimethoxyflavone.
- Seringolam, Werner Herz,Govindan, V.,Riess-Maurer, Ingrid,Kreil, B.,Wagner, Hildebert,et al.
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p. 669 - 672
(2007/10/02)
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